Toluene → Chrysene-2-carbaldehyde

HRID 2413602Notes

Reaction equation

HRID 2413602 reaction equation
[OH:1][CH2:2][C:3]1[CH:20]=[CH:19][C:18]2[C:17]3[C:8](=[C:9]4[C:14](=[CH:15][CH:16]=3)[CH:13]=[CH:12][CH:11]=[CH:10]4)[CH:7]=[CH:6][C:5]=2[CH:4]=1.C1(C)C=CC=CC=1>C(Cl)Cl>[CH:4]1[C:5]2[CH:6]=[CH:7][C:8]3[C:17](=[CH:16][CH:15]=[C:14]4[C:9]=3[CH:10]=[CH:11][CH:12]=[CH:13]4)[C:18]=2[CH:19]=[CH:20][C:3]=1[CH:2]=[O:1]

Participants

4

Reactant 2

HCID 1140TolueneHCID 155993232-Hydroxymethylchrysene

Product 1

HCID 15599322Chrysene-2-carbaldehydeYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Hydroxymethylchrysene (20C, 8.0 g, 0.031 mol) in CH2Cl2 (2.5 L) was treated with BaMnO4 (Aldrich, 15.9 g, 0.062 mol) and refluxed for 12 h. The reaction mixture was filtered, and concentrated to give a solid, which was then passed through a plug of SiO2 (500 g) using PhCH3 as the eluting solvent. The appropriate fractions were combined and the volume reduced to 75 mL to afford 6.98 g (88%) of chrysene-2-carbaldehyde mp 215°-216.5°, (C,H).

Workup

  1. temperaturerefluxed for 12 h
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated
  4. customto give a solid, which

Sources & evidence

ORD record
ord-e51f03fbb2a2427ca67ae091bd6a8a49
Source dataset
uspto-grants-1988_01
Patent number
US04719048

Reaction notes

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